| 18. Round | 31/07/2021 | Tulevik Viljandi | - | JK Tammeka | 5:3 | ||||
| 19. Round | 07/08/2021 | Paide Linnameeskond | - | Tulevik Viljandi | 3:1 | ||||
| 20. Round | 15/08/2021 | JK Nõmme Kalju | - | Tulevik Viljandi | 3:1 |  |
|||
| 21. Round | 20/08/2021 | Tulevik Viljandi | - | Pärnu JK Vaprus | 1:0 |  |
|||
| 22. Round | 27/08/2021 | Tulevik Viljandi | - | JK Tammeka | 4:1 | ||||
| 23. Round | 11/09/2021 | JK Narva Trans | - | Tulevik Viljandi | 1:0 | ||||
| 24. Round | 18/09/2021 | Tallinna JK Legion | - | Tulevik Viljandi | 3:1 | ||||
| 25. Round | 26/09/2021 | Tulevik Viljandi | - | FC Flora | 2:2 | ||||
| 27. Round | 16/10/2021 | Tulevik Viljandi | - | FCI Levadia | 3:2 |
Estonia